


Pretty

by orphan_account



Category: Supernatural
Genre: Crossdressing, M/M, Sibling Incest
Language: English
Status: In-Progress
Published: 2013-07-14
Updated: 2013-07-15
Packaged: 2017-12-20 03:54:26
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 3
Words: 4,908
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/882648
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>It starts with a dare to to trade clothes with Jess.</p>
            </blockquote>





	1. Chapter One

Maybe he would invest in some satin sheets. It wouldn't be the gayest thing he'd done since he'd officially come out; he could probably get away with it unscathed.

Not that the cool cotton he was currently wrapped in was anything to scoff at, of course. The soft drag of the material over his blood-warm skin was nothing short of rapturous in that moment. Then again, in that moment, he was also not a little bit inebriated.

It'd just been half midnight on Sunday when Sam rolled into bed after spending the weekend at Jess's house. His father would be home in the morning, and he would have been most displeased if he'd known what his youngest had been up to.

Sam scoffs to himself and flips onto his stomach, shirt rucking up and legs sprawling. It had been a great weekend. He'd gone home with Jess after school on Friday, the two juniors beyond excited about their plans for the next few days. Movies, alcohol, and one-on-one time they hadn't had in weeks since Christmas break. Of course, alcohol and slumber parties led to truth or dare, which led to trading clothes with Jess. Which somehow led to a fashion show, which in turn led to Sam shaving his legs below the knee. Which led to rutting lazily against his own sheets back at home, feeling sensual and soft with his newly bare skin.

He passes out before getting anywhere near completion, but sleeps satisfyingly heavy enough that it doesn't matter. And when Sam wakes in the morning to the worst morning wood he'd had since 7th grade, he doesn't think twice about blaming it on his silken appendages.

He spends the morning waking himself up properly, one hand down his boxer-briefs and another tracing ticklish lines over his torso, tossing around under the covers and arching near-painfully when he dips his fingers lower to tease his entrance.

Once he's come, he sighs and grins exuberantly in satisfaction, knowing his lips are bruised from biting back groans, and that his legs are smooth enough to rival any girl's.

He could get used to this.


	2. Chapter Two

Dean's always been a tactile person. Even as a toddler, waddling around the house on chubby, unsteady limbs, he'd navigated better by touch, always grasping at the hems of his mother's dresses and rubbing baby-soft palms over his father's salt n' pepper stubble with wide, curious eyes and ecstatic laughter.

As a teenager, he had been no different, tripping work-callused finger pads over tender skin and hard muscle alike. Platonic, romantic, or just exploratory, no one in Dean's company could expect to last long without an enthusiastic embrace, a grounding pat of solidarity, or at the very least, an elbow nudge. He spoke with broad hand gestures and a booming laugh, a boisterousness that most knew came from Mary's side of the family. His father had always been more reserved, more introverted. He never thought disapprovingly of Dean for his outgoing nature, however, just looked on with a quietly proud gleam in his eye.

As a 21 year old college dropout, Dean is continuing his hands-on lifestyle by working as a mechanic at a family friend's auto repair shop. He'd apprenticed (unpaid) with Bobby Singer throughout high school, and when his college courses failed to hold his attentions, he dropped out without batting an eye at 19. Tuition money would be better spent on saving up for an apartment, he'd decided, so he could be the first of his friends to be truly independent.

What he hadn't counted on was John losing his job.

So Dean stayed home, helping pay bills and take care of things around the house while their dad bounced from job to job, eventually finding a job at a steel mill two towns over. It was a long drive, and he often ended up crashing with a work buddy when he was working three-day shifts to save on gas, but the pay was good. In the meantime, the Winchester brothers were often left home alone for days on end, which was nothing to weep over, as far as they were concerned.

These stretches of unsupervised revelry resulted in the Winchester house becoming a haven amongst friends. It was rarely just the two brothers in the house; Sam's high school friends made the most of the parent-free environment to experiment with alcohol and co-ed sleepovers, not without aiding in cleanup, of course. Dean would invite a few girls (or the occasional guy) over, and Sam would just walk home from school with an entourage of friends excited to share in the freedom.

A lot of this changed when Sam came out. Dean had known, obviously, since Sam had whispered his insecurities to him in middle school. He was the only one of his friends who had never so much as had a crush on a girl, and Dean was there to reassure him and tell him he'd be okay. A few of Sam's high school friends, however, were far less accepting of his sexuality, the majority of whom were boys. Even the boys who didn't begrudge him his preferences unconsciously distanced themselves, until Sam was left with Jess and Andy. Even Andy had moved away during the summer after their sophomore year.

So Jess became a regular face in the Winchester household. Dean often picked on them just to see Sam blush, saying they were grow old and gray and single together. Jess would smack the back of his head and claim that he was just jealous, because Sam got her all to himself. Dean would toss his head back and laugh, calling her feisty, and join them in whatever they were doing.

Sometimes, though, Dean's presence was overwhelming. He was like a hot-burning light, filling the room with warmth and brightness until everyone was consumed by him. Sometimes Sam wanted the peace of Jessica's home, the distance from Dean that often proved therapeutic. At Jess's house, he could recline against her from the floor and let her practice French braiding on his hair and not be teased, because  _it feels good, Dean, shut up_ ; and he could ask her for advice about flirting, and trade stories about guys and geek out over Buffy without worrying about Dean thinking he was lame or campy. It was also refreshing to just get away sometimes, like Jess's house was cooler, calmer somehow. Everything around Dean was heat and excitement; he and Jess vibed with each other fantastically in that. They were both energetic and talkative, and when they were in the same room, there was never a slow moment or a peaceful quiet; every minute was filled to the brim with laughs and conversation and witty banter. Sometimes Sam wanted the boredom.

Like now, as he stretched back over her lap on her living room floor. There was a Doctor Who marathon, which Dean was watching from home and texting with Jess about. He was also texting Sam, trying to make him feel guilty for leaving him all alone in their big, empty house, but Sam just shrugged it off. If they were at the Winchester house, he wouldn't be able to hear the show over Dean and Jess's running commentary.

Jess had her fingers in her hair, and Sam was trying not to drift off to sleep. It was still Eccleston's season, and he loved the ninth Doctor. "Hey now," she started, tugging his hair sharply. "Don't you fall asleep. It's only five."

Sam groaned and rolled his eyes. "If you keep doing  _that_ , I can't be held accountable. You know it makes me sleepy." Jess pointedly removed her hand and pushed him off her lap.

"Let's go to your house," she begged. "Dean will be able to keep you up, and your dad isn't supposed to be home until tomorrow night anyway. And I need some testosterone exposure."

"You have me for that."

Jess snorts. "Please, you shave more of your body hair now than I do. When I dared you, I didn't know I was creating a monster."

This was true. Sam had relished the feeling of soft, bare skin so much that he'd taken it up a notch. "If it makes you feel better, I have razor burn in some seriously unsavory places."

"It does give me a vindictive pleasure," she sighed. "Still. I haven't nuzzled Dean's hard man pecs in  _days_ , Sammy, _days_." As if this settled the matter, she picked up her phone and started texting the Winchester in question.

Sam just groaned and rolled onto his stomach. "Tell him to bring alcohol, then."

"Duh."

 

**Notes for the Chapter:**

> all over the place filler. Sorry! still trying to work out where i'm going with this. 
> 
> Thanks for reading!


	3. Chapter Three

Dean arrives an episode and a half later, arms laden with alcohol and pizza. Sam and Jess are quick to help him, arranging everything on the island in the kitchen before taking stock of their spoils.

Dean saves them the trouble. "Two large pepperonis, one medium cheese for Jess, Smirnoff for mixing, Evan Williams for me." He grins at the stricken look on Sam's face. "What?"

"We're gonna puke everywhere, Dean." At this, Jess cheers and fetches the plastic cups. Her parents are on their second honeymoon for the week, and Jess is beyond ecstatic to be the party house in the meantime to mix things up.

"Did you bring coke?" she asks offhandedly, clearing a spot on the counter for paper plates and napkins.

Dean shakes his head. "I figured you had some here."

"I do, but it's half-gone and flat," she shrugs. "Oh, well. SHOTS!"

Dean got on board with that idea pretty quickly, and Sam let out a put-upon sigh. "I hate shots."

"You're not supposed to  _like_ 'em, Sammy," Dean remarks with a slap to his brother's back. "They just get the job done efficiently. And we can play drinking games with them."

"Drinking games!"

Sam groans. "I guess that's settled then." Jess lines up three cups and pours a portion of the Evan Williams in each, Sam whining at the amount and Dean whining that she used the bourbon.

"That's for my lonely nights!"

Jess punches his arm and shushes him. "You have Sam for your lonely nights. This is for shots!"

Sam blushes and nudges her in the arm, but Dean just chuckles and takes his cup. They tap their rims together before knocking them back, Sam and Jess spluttering while Dean just 'ahhh's.

"More shots!" Jess cries when they've regained their composure, but Sam goes searching for the flat two liter of Coke to mix his with.

"I don't wanna get too fucked up with Dean here," he explains with a frown. "I don't want him doing shit to me if I pass out."

Dean, at this, looks mock-affronted. "Sammy, I would never." Sam has picture evidence that proves otherwise, but ignores him in favor of mixing his drink.

Dean and Jess knock back two more 'shots' while Sam still sips on his drink. "Let's move to the living room," she orders, grabbing her pizza and leading the way. Dean forgoes the cups in favor of just grabbing the bottle and carrying it along with his pizza, and Sam follows.

They don't touch the alcohol for another episode, but by the time they've had their fill of pizza and coherence, they break it out again.

"Let's play truth or dare!" Jess cheers, feeling the effects of the bourbon.

"We always play truth or dare, and it always ends up the same," Sam groans.

"But Deanie baby hasn't played with us ever!"

"Deanie baby?" Dean laughs heartily at that. "Okay. I'm up for it if you are, Sam."

Sam feels victimized. "Fine." But he'll be a ruthless bastard about his dares.

Jess cheers and orders them into a triangle so they can all look at each other while they play. "Okay! Sam first!" She jabs a finger in his direction. "Truth or dare?"

"Truth."

"Pussy," Dean teases.

"Dick," Sam mumbles back.

"I dare you-"

"I said truth, Jess."

Jess sighs like Sam is some great inconvenience she must overcome. "Fine. Um…"

"Tick tock," Dean goads her. He gets a punch in the shoulder for his efforts.

"Okay. Sam. What was your last wet dream about?"

Sam turns scarlet to the roots of his hair. "Jesus, Jess, dive right in."

"We're gonna end up here anyway, so." She shrugs.

"Okay. Um." Sam is still blushing and refuses to make eye-contact with either of these assholes. "You can't laugh, okay?" He waits for their respective nods before continuing. "Okay. Well. It was… Jesus. It was in the back of a car," he starts, voice lowering with each word.

"And?"

"You asked what it was about, you didn't ask for details!" Jess groans and falls forward, head in her lap.

"That was a lame answer. Punishment shot!" Sam rolls his eyes, but complies nonetheless, knocking the bottle back to take a swig and gagging.

"Okay, Dean's turn!" she demands. "Dean, truth or dare?"

He smirks. "Dare."

"Ooh, ooh! I dare-"

"Jess, you just went. It's my turn to dare him."

She rolls her eyes. "Fine."

"I dare you…" Sam looks around and ponders the possibilities. "I dare you to… take three shots in a row, no breaks in between, then try to put on eyeliner." It seemed fitting, as Dean hardly seemed affected by the alcohol thus far. Sam was at the very least tipsy, and Jess was giggling her way to intoxicated.

Dean scoffs. "Hit me." Jess claps and runs to grab the cups so that she will be able to measure out how much he gets. Sam, being the (slightly) more sober of the two, is responsible for pouring them, and Jess boos at the amount he decides is fair. "Easy," Dean brags, reaching for the first cup.

One goes back and he doesn't flinch.

The second one results in a face scrunch and brief shudder.

The third one has him sticking out his tongue and gagging, but he gets it all done in under ten seconds. He spends six minutes in the bathroom before he comes back, eyes a smudged black mess, red and watery from irritation. "How do you do this shit."

Jess cackles and points, and he turns to fix her with a glare that would be far more intimidating if he didn't look like he got stood up at prom.

"Jess!" he manages. "Your turn, princess. Truth or dare?"

"Dare!"

"I dare you to go commando for the rest of the night."

"Done! Woo! I win!" Sam looks personally affronted and Dean lifts an eyebrow.

"You're not wearing panties?"

"Are you kidding, have you seen these jeans?" she giggles hysterically. "Next! Sam!"

Sam blinks owlishly and frowns. "Uh, dare."

"Dean! Dare him!"

"Um, I dare you…" Dean stares at him hard, thinking. Sam tenses in anticipation. "I dare you to shave your legs."

Jess falls backwards in a fit of giggles, rolling on the floor and smacking her hands against the carpet. Sam clears his throat and moves the bottle out of her reach. "Done," he mumbles.

Dean's brow creases. "What?"

"I, uh," Sam's never blushed so much in one night. He's probably gonna have an aneurism, and everyone's too drunk to drive him to the hospital. "I, uh, I already do that."

Jess is still shaking on the ground with laughter, wiping tears from her face.

Dean turns to her. "Firstly, you're cut off for the night." She just nods, knowing she's past her limit. "Secondly," he looks back to Sam. "Since when do you… shave your legs?"

Jess cackles. "Not just his legs!"

It is not possible to blush any harder, of this Sam is certain. Dean just blinks at this new information. "Really."

"Uh. Yeah."

"Huh." Dean takes another minute to process this. "Well, then, I dare you to go put on one of Jess's dresses."

Jess is positively in hysterics, rolling on the ground and kicking her legs. "HA! Sam…!"

Sam just says, "Fine," and stalks towards Jess's room. He picks out his favorite dress as of last week, a strapless white dress with yellow flowers and a full skirt, and lays it across the bed before stripping out of his clothes, which he piles by the door before slipping the dress up his slender legs. He has to lean against the bedpost for support, swaying tipsily while he wiggles the zipper up. He finally makes his way back to the living room, giving a twirl at the end of his trek for good measure, though he immediately regrets the decision when the world shifts under his feet. He catches himself on the wall with a chuckle and faces Dean.

Dean looks stricken. His eyes are wide and his jaw is dropped, and suddenly Sam just wants to hide. He feels blistered by the abruptness of his shame, more aware by the second of how quiet the room has gone. "Shit, Sammy," Dean whispers, still not averting his eyes, and Sam bites his lip. This was a bad idea.

His fingers clench in the fabric around his thighs and he looks away, eyebrows drawn in frustration and embarrassment. Dean thinks he's a freak now. His faggot baby brother walking around in girls' clothes like it's second nature, shaven bare like a practiced girl, blushing like one, too. He closes his eyes and turns, heading back to Jess's room. Once he's there, he slams and locks the door behind himself, tugging at the zipper and removing the dress as inelegantly as possible, just wanting it off.

He liked the dress because it made him feel attractive and empowered. He'd been able to feel his silky smooth legs brushing together, and the soft material of the skirt shifting against his skin made him feel so subtly and intensely sexual in ways he hadn't before. He'd never felt so good and self-assured as he did in someone else's clothes, and he should've known there was something wrong with that right off the bat.

Of course Jess wouldn't have said anything; she's his best friend. She would never tell him to his face what a freak he was. She's too sweet. But now Sam can feel it, right down to his bones, the  _wrongness_  of it. It had been written all over Dean's face and in the silence of the room.

It was just a dumb dare. He shouldn't feel this sick over it. He should be able to play it off like it's no big deal, like he's just paying his dues. But he knows that it's deeper than that, and he knows that  _Dean_ knows, too; that Dean can tell this wasn't the first time, and probably not the last, that Sam had worn Jess's clothes. It was obvious in his easy movements, in how the dress sat on his frame.

It's not like he wants to be a girl. He _doesn't_. He just likes the way the clothes make him feel. It's something he can do for himself, to make himself feel good. It's not like he's gonna start wearing makeup and wigs. It's just the clothes, and just sometimes.

Sam kneels down by the bed, still divested of clothing, and buries his face in the comforter.

 _Fuck._ His eyes sting and his throat feels tight. He shudders and feels his eyelashes, suddenly wet, brush against the material pressed to his face.  _Great_ , he thinks.  _Now I'm gonna cry like a girl, too_.

A knock on the door goes barely noticed. "Sammy?"

Sam doesn't respond, not acknowledging the jiggling handle. "Sammy, are you okay?"

The door continues to jiggle for a moment before a heavy sigh is heard from the other side of the door. "I didn't… I'm sorry for staring, Sammy," Dean tries. "I just… I wasn't expecting that. Please don't be mad."

Sam's lips tremble and he hiccups a little into the mattress.

"Sammy, I'm sorry," Dean says again. "You… you just… you looked so pretty."

The younger brother growls. "Shut up."

"Hey!" Dean sounds relieved that he replied. "Sam, come open the door. I wanna talk to you."

"No."

Dean sighs again, and a thump lets Sam know that Dean has dropped his forehead to rest against the white-painted wood of the door. "Sammy, come on. Jess is passed out back there. Let's at least put her in bed, and then… I'll leave you alone if you want."

Sam takes a few moments to turn this over in his head. He pulls himself up until he's at a right angle, head still rested on the mattress and legs stick straight, before slowly pushing up his torso, too.

He opens the door and ignores Dean almost falling through, keeping his eyes on the floor and pushing his way out into the living room.

He stumbles over the pizza boxes and falls onto the couch, and lies there for what feels like a few seconds but must be longer, because when he opens his eyes again, Jess is gone from the floor, and Dean is stretched out on his back in her place, watching him.

"Hey-a, Sammy," he whispers. The lights have all been turned out, and Sam feels a rolling nausea when he lifts his head.

"What time is it?" he slurs.

Dean checks his phone from somewhere to his right and replies quietly, "1:13."

"Fuck," Sam hisses. "I think…" he swallows a few times, hearing the dry click of his throat. "Think I'm gonna…" Dean is quickly on his feet, one hand rolling Sam onto his back and another sliding under him to slowly lift him into a sitting position.

"You need to throw up?"

Sam nods, immediately regretting it, and groans, clinging to his brother's forearms. Dean wraps his arms around his little brother's skinny torso, pulling him gently to his feet, and helps him pad along to the hall bathroom. Sam immediately drops to his knees and rests his forehead against the cool surface of the toilet, a decision the sober part of his consciousness is berating him for, and the drunken part of him is beyond grateful for.

"I just wanna throw up," he groans miserably. "I'll feel better, I just… I wanna…" he's panting now, breaths coming deep and fast, saliva flooding his mouth.

Dean trails his fingers up and down Sam's back, touch becoming more firm as Sam starts to gag.

"I know, baby brother," he murmurs. "Just get it out."

When he finally vomits, Sam's whole body tenses with it, stomach rolling and toes curling. It takes him a few heaves, but he feels infinitely less nauseated once his belly is finally clear of the heavy pizza and alcohol combination.

"There we go," Dean mutters, a cool, wet rag appearing from nowhere to wipe the traces of vomit, tears, and sweat from Sam's face. "Much better, huh?"

Sam just chokes out a wet groan and falls forward into his brother, still unaware of how little he's wearing.

"'M sorry, Dean," he whines.

"Shhh…" Dean's arms wrap around his body, cradling him to his warm chest and stroking his back. "Nothin' to be sorry for, Sammy."

Dean continues rocking him in place until Sam's body goes slack, finally asleep again.

When Sam wakes up, he's back on Jess's couch, fully dressed and covered with a heavy blanket.

His knees are sore, probably from hitting the tile of the bathroom last night, and his throat is raw. "Dean?" he tries, but it comes out cracked and dry.

He can smell coffee, and he winds his way into a standing position as steadily as he can and ventures into the kitchen. Jess is resting her head on the counter, watching the coffee drip down into the pot, and Dean is in the shower, from what Sam can hear.

"G'morning," Sam grunts, joining Jess in watching the percolator.

"No," she groans. "So bad."

He nods vacantly and accepts the proffered ibuprofen when she holds it out to him. "What time 's it?"

"11:30." Again, he just nods. "Dean got up first. Woke me up with water and the ibuprofen. He's the one who made the coffee. In the shower." She looks exhausted just from saying this much.

"Okay." Secretly, he's glad Dean made the coffee. Jess always makes it too weak. "Last night was awful."

Jess whines. "So awesome at first, though. 'Till you went and drama queened out on us."

Sam scowls. "I'm sorry, but who outed my biggest secret to my brother?"

She rolls her eyes, wincing as it irritates her headache. "Please. Dean doesn't care about that shit."

"Did you see his face?" Sam lowers into a chair at the island. "He was so freaked."

"He loved it," she retorts. "You just wouldn't stick around to hear 'im say it."

Sam scoffs inwardly. "What d'you mean, loved it?"

Jess finally reopens her eyes to meet his gaze with something like pity. "Nothing. Coffee's done."

Sam lets it drop and fishes out three cups from the cabinet behind him while Jess grabs the creamer from the fridge. She's the only one who uses it, because Sam might be gay, and he might occasionally wear girly clothes, but he takes his coffee like a man.

"Coffee done?" Dean walks into the kitchen in nothing but his jeans from last night, wet hair still dripping water in rivulets down his skin. Jess hums appreciatively at the sight.

"Yup. God, I love you." She pours both of the Winchesters a cup before fixing her own drink, loading it with sugar and cream. Sam's stomach rolls at the smell, and he buries his head in his arms. Once her drink is fixed, Jess wanders to where Dean is sipping his coffee against the counter and leans into his chest, nuzzling his sternum fondly as he chuckles.

Sam clears his throat and turns his head over to face the opposite wall. He knew that their feelings were platonic, but that didn't stop the sight from disturbing him. "Aw. You jelly, Sammy baby?" Jess teases.

"Fuck off," he mutters. "'M too hungover for this shit."

"Wow," she replies, sounding wounded. "Feeling rude?"

He sighs. "Sorry."

"I know." She pushes off from Dean's chest, causing him to grunt, and makes her way over to Sam before running her fingers through his hair. "You're okay, Sam," she whispers into his ear before kissing the hair above it softly. "I'm gonna go shower," she announces to the room at large, having drained her coffee and eager for the brothers to sort out their shit.

"You do that," Dean replies. "I'll get Sammy fixed up."

"I don't need fixing," Sam retorts.

"Right." A hand lands softly between his shoulder blades, big and warm. Dean's thumb presses into the muscle along his spine, and who is Sam to deny a massage? He moans and settles more heavily against the counter, resisting the urge to tense his muscles by arching into the touch.

Dean laughs quietly and sets down his coffee, moving fully behind his brother and setting both hands to work, leaving Sam a barely-coherent lump.

A few minutes pass before Sam speaks up. "Dean?"

"Hmm?"

How is he supposed to word this? How do you apologize for acting like a girl without sounding like a girl, while explaining that while you occasionally dress like a girl, you don't want to be one? "I… I guess I'm sorry? About last night?"

Dean's hands still on his back. "What for?"

Sam sighs. "I... So… you know, obviously, I guess, that last night wasn't the first time I wore Jess's clothes," he tries.

Dean rubs his right hand across his shoulders. "I figured that much out."

Sam rolls his lips in, biting them between his teeth. "So… I… it's been happening? For like… a month or so."

"Okay."

"Yeah. But not like… like I don't want to be a girl, or anything," he insists. "I just… there's something about the way the clothes feel? I don't know, this is so stupid…"

"Not stupid, Sammy," Dean murmurs, hands back to work fully.

"And weird," Sam continues. "But… I don't know. They make me… feel… good. About myself, I mean."

"That's okay."

"No, it's not." Dean's hands stop again.

"Yes, it is, Sammy. You can do whatever you want.  _Whatever_ you want. You could be like, super into dressing up like a mascot to have sex and being a furry or whatever, and that would still be okay."

"I'm not."

Dean chuckles. "I know you're not into mascot sex. But you get where I'm going."

Sam blinks. "Yeah. I guess."

"So you know I don't care. Well, I  _do_  care. But not like, in a bad way. I care about you being happy."

"Yeah."

"Okay. Good." He's done with the massage by now, so his fingers just trail across Sam's back, borderline ticklish. "And Sammy?"

Sam closes his eyes and sighs. "Mhmm?"

Dean says nothing for a moment, as if searching for the right words, before, "You really did look good like that. I mean it."

There's something so certain about the way he says it. It doesn't warrant a reply, so they both just endure the moment quietly, listening to the faint sounds of the shower running and smelling the coffee as it burns.

When Jess finally rejoins them, they're both sat at the island, smiling softly between sips of coffee, and her heart fills with the sight of her boys, finally getting somewhere.

She turns on the kitchen radio and starts another pot.


End file.
